Ben Gibbard's first solo album Former Lives is a surprisingly upbeat affair, with a focus on storytelling and less of the intense, corner-of-the-garage introspection you've come to expect from his day job as frontman of Death Cab for Cutie. Four years ago Gibbard stopped drinking and became addicted to marathon running instead. But his former life – as a youth in Washington at the height of grunge, as a collaborator with diffident musical types Jay Farrar and Jimmy Tamborello, as husband to Zooey Deschanel – is still rich pickings. Which is why we asked for the five defining songs of his career.

I wrote this song at a time of real transition. We'd grown up in a sleepy little college town called Bellingham, an hour and a half north of Seattle: everything was simple, living is cheap, you don't have to worry about tomorrow. Then we moved to Seattle and suddenly everyone's life became terribly spread out. I was mournful of the fact I was not as physically close to the people I loved – everyone was trying to figure out who they were, trying to make enough money to live. We'd reconvene at our bass player Nick's mom's house in the suburbs. She was working on a PhD at that time and up all night studying, but she was so supportive – all our parents were – letting these scruffy musicians into their houses, moving the furniture around to set mics up. I've never forgotten the support they gave us.

This is about a weird dream I had when I was 24 involving Evan Dando and Chan Marhsall [Cat Power]. It was completely G-rated, not one of those inappropriate dreams, but it was bizarre – you know, in the same way you dream that you're in your house but it's not your house, your friend is there but he's a merman. The song was a collaboration with Jimmy Tamborello [AKA Dntel] and it led to our full-length album a couple of years later as the Postal Service.

I was approached to do some work on the soundtrack for a movie about Jack Kerouac [One Fast Move Or I'm Gone] with Jay Farrar, this wonderful, mysterious Americana songwriting legend – he used to be in Uncle Tupelo with Jeff Tweedy. Kerouac has inspired me since I was a teenager. I gave up drinking three years ago after a trip where I tried to "recreate" the novel Big Sur. I could see how On the Road was all about not having a care in the world, allowing the long nights and excesses to define you in the positive the way most people do when they're young. But Big Sur was the proverbial end of the road, and it showed me how that kind of lifestyle can end in alcoholism. There's footage of Kerouac at the end of his life when he's a horrible drunk and really embittered; I found myself in literally the same place, staying in a cabin he'd stayed in and knowing how it ended because I had read the book. Big Sur is the most beautiful place in the US, but when you're in a disturbed emotional state the vastness of it was upsetting – it felt like evil spirits were lurking there. I've been back to that cabin a number of times and once again it looks beautiful, and I wonder how I could ever have felt so unsettled.

This is from a really dark record we made in 2008 [The Narrow Stairs] and I'm proud of it, but I feel I've written all I can from that emotional palette. While The Employment Pages is very much a construction project, where we tracked one part at a time, on this song we recorded all the tracks together and it became this eight-and-a-half-minute beast. When Nick came in and brought that bass line I thought, I never want to stop playing this – it felt so good to drop these little bits of guitar and piano in, so propulsive. It's one of the things that attracts me to krautrock, whether it's Can or Neu – it becomes so hypnotic and meditative. It was 10 minutes long originally.

This is from the new record. It's my tribute to the Smith Tower in Seattle, which was built in 1914. Up until the 30s it was the tallest building west of the Mississippi River, then they built the Space Needle and now that's all anyone ever talks about – it's become the symbol of the city. The song personifies the tower as this once great thing, crying metaphorically, and literally, because there are actual teardrop-shaped windows at the very top. But the interesting thing is, there's an apartment up there too, with this woman living in it – the New York Times did an amazing pictorial. I've heard she's planning on inviting me up to dinner. It looks like the kind of place a superhero would live. We've actually got a superhero in Seattle by the way, a guy called Phoenix Jones who goes around town dressed up in a costume with a can of Mace, breaking up fights and acting out vigilante justice. I am not making this up.